It always struck me as so strange that Oliver Stone, when he was making his name with Platoon and Wall Street, saw Charlie Sheen as his ideal everyman, the audience representative, the proxy, the innocent surrounded by the rot and corruption Stone sees around every corner. Even then, before the drugs and the porn stars and that ghastly skin color and the rotted teeth, Sheen was anything but "normal." Even the fans who love him—a large percentage of which are baseball players; I loved that during his bitchin'-rock-star-from-Mars meltdown of two years ago, he kept calling into The Dan Patrick Show and hanging out with Brian Wilson—see him as some sort of ideal male id, the manifestation of how all men would act if everything were stripped away, if nothing mattered.

I don't find Sheen particularly fascinating, but I do understand the appeal: As Entertainment Weekly's underrated film critic Owen Gleiberman put it, his nationally televised implosion was "an addictive prospect, a slumming form of performance-art entertainment for an overly controlled, rule-bound, PR-driven, terminally politically correct, spin-cycle America." His lunatic act carried with it the hint of wish fulfillment: This is what batshit looked like, and while it looked like death, it looked like not the worst possible way to go.

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The problem, of course, is that Sheen didn't die, that he kept living, taking all the fun out of it. And all that apparent appeal makes him, perhaps predictably, pretty terrible at playing anyone other than Charlie Sheen. His first big movie role since leaving Two and a Half Men and going nutty, Charles Swan (originally titled A Glimpse Inside the Mind of Charles Swan III), opens in theaters this Friday (it's already available on demand), and, suffice it to say, Sheen is about as capable of playing a character who isn't Charlie Sheen as he is of playing a dog, or a muffin, or a bottle of shampoo.

The movie, written and directed by Roman Coppola (Wes Anderson's co-writer on Moonrise Kingdom, son of Francis, brother of Sofia, cousin of Nicolas Cage and Jason Schwartzman), is a shambling "portrait" of a neurotic art director in the '70s named Charles Swan III, played by Sheen, who can't get over his ex-girlfriend. That's pretty much the whole movie. Swan's a loafing trainwreck mope with a "wild" imagination that allows Coppola to indulge himself through various fantasy sequences, none of which adds up to much of anything. Coppola has made only one other film but has directed various videos for The Strokes and Phoenix and other too-old-to-be-hip-anymore bands, and his film has the lazy, meandering, look-who-I-got-to-be-in-my-movie! entitlement you'd expect. Imagine if Sofia Coppola's movies were all about male insecurity, except more smug and a lot more poorly directed. Sofia can create a mood as well as her father, even if she doesn't always know what to do with the skill; Roman is too interested in posing to create much of anything. Coppola consciously tries to mimic Wes Anderson's whimsy and archness, but he lacks control of his instrument. He can't figure out the right tone, so the whole thing ends up feeling like a disorganized celebrity roast. (If you're a Wes Anderson hater, just watch this film, and you'll get a new appreciation for his abilities. This is what happens if someone who isn't Wes Anderson tries to make a Wes Anderson film.)

The movie is full of missteps and pointlessness—Coppola has Aubrey Plaza and Mary Elizabeth Winstead in his movie but barely gives them any lines—and wouldn't have any reason to exist at all if it weren't for its cast. Cousin Schwartzman shows up just to mug and preen; Stephen Dorff pops in because of course he does; and, worst of all, Bill Murray, looking confused but still game, plays Swan's accountant/business manager, Saul. Look, Bill Murray Stories are charming and all, but the downside to Being Bill Murray, Quixotic Wanderer of Earth is that sometimes you quixotically wander into something idiotic. (Other recent examples: Passion Play and Get Low.) Fortunately, he's Bill Murray, so no one cares.

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But Coppola's worst decision was casting Sheen, who can't shake off his sitcom rust to play a real character. Charles Swan is supposed to be neurotic and self-questioning, but Sheen is perhaps the least neurotic and self-questioning person on earth; hearing him say, "I'm still in love with her, man" and "I guess I'm gonna die alone" is about as convincing as, oh, Courtney Love playing John Candy. Sheen wears a stupid wig and dark sunglasses throughout the film, looking ridiculous for ... well, I'm not sure why, exactly. He appears to be a reflection of the director and a commentary on male-female relations, but Coppola can't even tap into Sheen's personal issues with women. You can just tell that Sheen took a slug of tequila and barked, "That work? Good. Next scene!" every time Coppola yelled cut. It's an empty performance in an empty movie. It's not even fun stunt casting. Sheen seems to have no idea what movie he's in, which, hey, I get it, I don't know what the hell this movie is either, man.

Grierson & Leitch is a regular column about the movies. Follow us on Twitter, @griersonleitch.